WO1998013035A1 - Preparations percutanees - Google Patents
Preparations percutanees Download PDFInfo
- Publication number
- WO1998013035A1 WO1998013035A1 PCT/JP1997/003412 JP9703412W WO9813035A1 WO 1998013035 A1 WO1998013035 A1 WO 1998013035A1 JP 9703412 W JP9703412 W JP 9703412W WO 9813035 A1 WO9813035 A1 WO 9813035A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- molecular weight
- tert
- chloro
- butylamino
- acid
- Prior art date
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/137—Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine or methadone
Definitions
- the present invention relates to a transdermal preparation of 2-tert-butylamino-11- (2-chloro-1-4-hydroquinphenyl) ethane-1-ol or a pharmacologically acceptable salt thereof (hereinafter, referred to as the present compound).
- the present invention relates to a transdermal preparation for percutaneous administration, and more particularly, to a transdermal preparation having excellent skin adhesion when applied to the skin surface and capable of maintaining the effective blood concentration of the compound for a long time.
- This compound excellent A Dorenari emission property / S 2 - Ri compound der having a receptor stimulating effect, the prevention of such dysuria such as impending flow, premature labor or urinary incontinence, it is known to be useful in the treatment (Japanese Patent Publication No. 7-111989).
- An object of the present invention have excellent A Dorenari emission property / 8 2 - the compounds used is a compound having a receptor stimulating effect, excellent KawaHiroshi permeability of the compound, the effect of JiMitsuru manner side effects
- the present invention is to provide a transdermal preparation useful for prevention and treatment of premature birth or dysuria.
- the present inventors have conducted intensive studies to achieve the above object, and as a result, formulated the present compound into a pressure-sensitive adhesive comprising a specific acrylic polymer or a high molecular weight rubber component-containing material and a specific additive.
- Percutaneous absorption-type preparation in which a progeny layer formed on one side of a support is obtained, good percutaneous absorption of the present compound is obtained, the effect is maintained for a long time, and a percutaneous absorption-type preparation
- the present inventors have found that side effects such as tremor and palpitations associated with a rapid increase in blood concentration are reduced, thereby completing the present invention.
- the present invention is as follows.
- a plaster layer containing the present compound and an adhesive is provided on one side of a support, and the adhesive is an acryl-based polymer substantially containing no carboxyl group, or Is at least one kind of high molecular weight rubber component containing an average molecular weight of 300,000 to 2,500,000, an ester of a fatty acid having 12 to 18 carbon atoms, and 8 to 10 carbon atoms.
- a transdermal preparation comprising at least one additive selected from the group consisting of monoglycerides of fatty acids and esters of dibasic acids having 6 to 10 carbon atoms.
- the acrylic polymer is at least one selected from 2-ethylhexyl acrylate, hydroxyshethyl acrylate, methyl methacrylate, 2-acryloxy methacrylate, vinyl acetate, and vinylpyrrolidone.
- high molecular weight rubber component-containing substance has an average molecular weight 5 0 0-4 '0 0 0 low molecular weight Poryi isobutylene or polybutene, and Roh or average molecular weight 1 0, 0 0 0-2 0 0' 0 0 molecular weight in the 0 With polyisobutylene, average molecular weight 300,000-2,500,
- the percutaneous absorption-type preparation according to ⁇ circle around (1) ⁇ which is a mixture comprising a high-molecular weight polyisobutylene of 0.000.
- transdermal preparation of claim 2 which is a fatty acid salt of 8 to 18 carbon atoms of 2-tert-butylamino-1- (2-chloro-4-hydroxyphenyl) ethane-1-ol.
- transdermal preparation according to ⁇ 1> further comprising a basic pH regulator in the plaster layer.
- transdermal preparation according to ⁇ which is an agent for the treatment of premature birth.
- the percutaneous absorption-type preparation according to ⁇ 1> which is a therapeutic agent for dysuria.
- a pharmaceutically effective amount of 2-tert-butylamino-1 as described in 1- (2-Chloro-4-hydroxyphenyl) ethane-1-ol or its pharmaceutically acceptable salt is administered transdermally to the patient A method of treating dysuria.
- FIG. 1 is a graph showing the change over time of the accumulated permeation amount of the present compound.
- FIG. 2 is a graph showing the change over time in the accumulated permeation amount of the present compound.
- An acryl polymer which is one of the pressure-sensitive adhesives used in the present invention has a carboxyl group. It does not react with the present compound because it does not contain, it has excellent drug release properties and excellent stability, and has properties such as giving better sustainability.
- the acryl-based polymer substantially containing no carboxyl group refers to an acryl-based polymer obtained by polymerization using a monomer having a carboxyl group modified such as acrylic acid / methacrylic acid. .
- acryl-based polymer examples include a homopolymer of an alkyl acrylate or an alkyl methacrylate, and a copolymer thereof.
- the alkyl in the alkyl acrylate or the alkyl methacrylate is a linear or branched alkyl having 1 to 18 carbon atoms, and specifically, methyl, ethyl, propyl, butyl, Examples include pentyl, hexyl, heptyl, lactocinole, 2-ethylhexyl, nonyl, isononyl, decyl, pendenyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, and octadecyl. Preferably, it is a linear or branched alkyl having 4 to 12 carbon atoms.
- acrylic polymer used in the present invention a copolymer of the above-mentioned alkyl acrylate and Z or alkyl methacrylate with one or more of the following monomers is also preferably used. can do.
- Examples of the simple S form include hydroxy lower alkyl acrylates (eg, hydroxymethyl acrylate, hydroxyshethyl acrylate, hydroxypropyl acrylate, hydroxybutyl acrylate), acrylamide, acrylamide derivatives (eg, , Dimethyl acrylamide, N-butylacrylamide, N-methylol acrylolamide, N-methylolpropane acrylolamide, aminoalkyl acrylate (eg, aminoethyl acrylate), acrylic Alkylaminoalkyl esters (eg, dimethylaminoethyl acrylate, tert-butylaminoethyl acrylate), alkoxyalkyl acrylates (eg, methacrylic acid acrylate) Tel, Ethoxylic acid acrylate), tetrahydrofurfuryl ester acrylate, an ester of acrylic acid and methoxydiethylene glycol, an ester of acrylic acid and methoxypolyethylene glyco
- the alkyl acrylate and / or the alkyl methacrylate 30 are used. It is desirable to copolymerize in a proportion of 99.5% by weight, preferably 50 to 90% by weight, and 0.5 to 70% by weight, preferably 10 to 50% by weight of the monomer.
- Ataryl polymer examples include 2-ethyl acrylate acrylate. And a copolymer of at least one selected from the group consisting of hydroxyxethyl acrylate, methyl methacrylate, 2-methoxyl acrylate, vinyl acetate, and vinylpyrrolidone.
- a copolymer consisting of 70 to 95% by weight of 2-ethylhexyl acrylate and 5 to 30% by weight of hydroxyxethyl acrylate or 60-95% by weight of 2-ethylhexyl acrylate A copolymer consisting of 90% by weight and 10 to 40% by weight of methyl methacrylate; 30 to 70% by weight of 2-ethylhexyl acrylate; and 2 to 50% by weight of 2-methylquinethyl acrylate % And vinyl acetate 10 to 50% by weight, and a copolymer consisting of 50 to 90% by weight of 2-ethylhexyl acrylate and 10 to 50% by weight of vinylpyrrolidone. And a copolymer comprising 30 to 80% by weight of 2-ethylhexyl acrylate, 10 to 40% by weight of methyl methacrylate, and 3 to 30% by weight of 2-methoxyl acrylate. I can do it.
- the high molecular weight rubber component-containing material which is another adhesive used in the present invention, comprises a high molecular weight rubber component having an average molecular weight of 300,000 to 2,500,000, There is no particular limitation as long as it does not adversely affect the release and stability of the compound.
- the high molecular weight rubber component is an essential component for imparting cohesive force suitable for adhesive bonding to the adhesive, and is preferably contained in the high molecular weight rubber component-containing material in an amount of 10% by weight or more. It is more preferably at least 20% by weight. If this component is not contained, glue will protrude from the periphery of the preparation at the time of application, and there is a high possibility that glue will remain on the skin surface upon removal.
- a resin such as a resin, a polyterpene resin, a coumarone-indene resin, a petroleum resin, a terbene phenyl resin, a xylene resin And a tackifier such as a fat-Hunch saturated hydrocarbon resin.
- the high molecular weight rubber component contained in the high molecular weight rubber component content used in the pressure-sensitive adhesive of the present invention specifically, polyisobutylene, polyisoprene, polybutadiene, styrene-isoprene-styrene block copolymer (SIS), styrene One pig Gen-styrene block copolymer (SBS) and the like can be mentioned, and these can be used as one kind or as a mixture of two or more kinds.
- polyisobutylene, polyisoprene, polybutadiene, styrene-isoprene-styrene block copolymer (SIS), styrene One pig Gen-styrene block copolymer (SBS) and the like can be mentioned, and these can be used as one kind or as a mixture of two or more kinds.
- polyisobutylene as an adhesive component from the viewpoints of interaction with a drug, release property, and the like.
- the average molecular weight is 300, 000 to 2,500 as an essential component. It contains high molecular weight polyisobutylene having a mean molecular weight of 100,000 to 200,000, and a medium molecular weight polyisobutylene and / or a mean molecular weight of 500 to 4.0000. It preferably contains low molecular weight polybutylene or polybutene.
- the high molecular weight polyisobutylene is 10 to 80% by weight, preferably 20 to 70% by weight
- the medium molecular weight polyisobutylene is 0 to 90% by weight, preferably 10 to 80% by weight. It is desirable to blend the polyisobutylene or the polybutene with a molecular weight of 0 to 80% by weight, preferably 10 to 60% by weight.
- the average molecular weight is a viscosity average molecular weight calculated from Flory's viscosity formula.
- the compound when a high-molecular-weight rubber component-containing material is used as an adhesive, the compound facilitates the diffusion of the compound in the growth body layer, obtains a good release property, and has an appropriate In order to obtain adhesive strength, it has excellent compatibility with adhesives, sufficiently dissolves this compound, does not cause separation of the adhesive components and additives over time (blueming), and has adhesive properties and Additives that do not adversely affect release properties, namely esters of fatty acids with 2 to 18 carbon atoms, monoglycerides of fatty acids with 8 to 10 carbon atoms and esters of dibasic acids with 6 to 10 carbon atoms At least one additive must be added.
- esters of fatty acids C, ⁇ C, the C ⁇ C fatty acid hexyl, Mi Risuchi phosphate (CM) isopropyl, Bruno Remichin acid (C IE) isopropyl, etc., to lauric acid (C 1 2) specifically. And esters with alkyl.
- As ⁇ Noguriseri de fatty specifically, the force prills acid (C.) Monoguriseri de force purine acid (C 1 0) Monoguriseri C 8 ⁇ C, such as de,.
- Monoglycerides of fatty acids and the like can be mentioned.
- the dibasic acid ester include C 6 to c, such as diisopropyl adipic acid (c 6 ), dioctyl adipate, and sebacic acid (C,.) Getyl. Esters of dibasic acid with di (d-c,.) Alkyl are mentioned.
- alkyl examples include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexynyl, nonyl, isononyl, and decyl.
- isopropyl myristate as a fatty acid ester is preferable, and more preferably, isopropyl myristate is used.
- the additive is desirably added in the range of 5 to 50% by weight, preferably 10 to 40% by weight, and more preferably 20 to 40% by weight in the plaster layer.
- amount of the additive is less than 5% by weight, there is a tendency that sufficient transdermal absorption of the present compound cannot be obtained.
- amount exceeds 50% by weight the cohesive force of the plaster decreases.
- glue remains on the skin surface during application.
- the compound of the present invention in the blue body layer (the compound of the present invention has an asymmetric carbon in the molecule, and there are two types of optical isomers, (1) rest and (+) isomers.
- (1) -form and (sat) -form having pharmacological activity are preferably used, and the compound can be produced by a method known per se.
- the present compound as an embodiment of a pharmacologically acceptable salt includes an acid addition salt or an alkali addition salt that can be produced by a conventional method.
- Acid addition salts include, for example, inorganic acid salts with hydrochloric acid, hydrobromic acid, hydroiodic acid, nitric acid, sulfuric acid, phosphoric acid, etc., or acetic acid, maleic acid, fumaric acid, citric acid, oxalic acid, lingoic acid Organic acid salts with acids, methanesulfonic acid, p-toluenesulfonic acid, mandelic acid, 10-carboxylic acid, tartaric acid, succinic acid and the like.
- alkali addition salt include salts with sodium, potassium, calcium and the like.
- a specific fatty acid salt having enhanced lipophilicity of the present compound can be used as another organic acid salt.
- Such fatty acids have lipophilic properties suitable for transdermal absorption It is preferred that it has 8 to 18 carbon atoms in view of the fact that it has a molecular size suitable for percutaneous absorption, and the like.
- the compounding amount of the present compound is usually 1 to 30% by weight, preferably 3 to 20% by weight, more preferably 5 to 10% by weight in the plaster layer.
- the amount is less than 1% by weight, it will be difficult to obtain the blood concentration of the compound required for treatment. If the amount exceeds 30% by weight, the adhesiveness will be reduced and sticking to the skin will be difficult. It tends to be difficult.
- the thickness of the descendant body layer having the above configuration is preferably from 20 to 100 im, in order to withstand long-term application to the skin captive and to prevent adhesive residue from remaining on the skin surface upon removal. 10 to 50 m is more preferable.
- the plaster layer may contain, if necessary, cunic acid, lactic acid, gluconic acid, triethanolamine, triisopropanolamine, ethylenediamine, triethylamine, ammonia, sodium hydroxide, potassium hydroxide, etc.
- Various known additives such as a filler such as zinc oxide and hydrous silicon dioxide may be blended.
- the salt of the present compound is liberated in the blue body layer to form a base.
- a basic PH regulator such as triethanolamine, trisopropanolamine, sodium hydroxide, or the like
- the salt of the present compound is liberated in the blue body layer to form a base.
- This compound is an embodiment of the present invention, whereby lipophilicity is enhanced, and good transdermal absorbability can be obtained.
- the basic pH regulator to be added is added with an amount (equivalent) necessary for neutralizing the acid added to the present compound which is in the form of a base. If the amount is less than the equivalent, good transdermal absorbability may not be obtained.On the other hand, if the amount is more than the equivalent, the descendant layer becomes basic, When sticking a skin-absorbing preparation to skin seedlings May cause skin irritation.
- the support used in the transdermal preparation of the present invention is not particularly limited as long as it can form and support a Xu body layer containing the present compound on one surface thereof. Additives that are lost from the back surface through the support and do not cause a decrease in content or efficacy, that is, those composed of an impermeable material are used, especially when applied to the skin surface It is preferable that the material has the flexibility to follow the movement of the skin surface to the extent that it does not cause discomfort.
- polyolefins such as polyethylene and polypropylene
- polyesters such as polyethylene terephthalate, polyvinyl acetate, ethylene-vinyl acetate copolymer, polyurethane, polyvinyl chloride, plasticized polyvinyl chloride, plasticized polyvinyl acetate
- Plastic films such as vinyl copolymers, polyvinylidene chloride, polyamides such as nylon, cellulose acetate, ethyl cellulose, ethylene ethyl acrylate copolymer, polytetrafluoroethylene, ionomer resin, etc., aluminum foil, tin
- a single-layer film made of gold foil, nonwoven fabric, cloth, paper, or the like, or a laminated film of these can be used.
- the thickness of such a support is usually in the range of 5 to 500 ⁇ m, preferably 5 to 200 ⁇ m.
- these supports are preferably subjected to a corona discharge treatment, a plasma treatment, an oxidation treatment, or the like, on the surface on which the paste layer is laminated, in order to improve the adhesion to the paste layer and the shrinkage.
- the method for producing the transdermal preparation of the present invention is not particularly limited.
- the present compound and an adhesive are dissolved or dispersed in a solvent, and the obtained solution or dispersion is applied to one surface of a support, and dried. And a method of forming a body layer on the surface of a support.
- the above solution or dispersion is applied on a release liner for protection, dried to form a solid layer on the release liner, and then the support is adhered to the plaster layer. Can also be manufactured.
- the percutaneous absorption preparation of the present invention may cause nursing eyebrows during production, transportation or storage. Cover the exposed surface of the plaster layer with a release liner until just before application to the skin, to prevent adhesion to instruments, containers, etc., and to prevent deterioration of the preparation. It is desirable to protect. Then, it is separated at the time of use to expose the surface of the plaster layer, and is applied to the skin for administration.
- the release liner is not particularly limited as long as it can be easily separated from the paste layer at the time of use.
- the release liner is formed by applying a silicone resin, a fluororesin, or the like to a surface in contact with the paste layer.
- Polyester, polyvinyl chloride, polyvinylidene chloride, polyethylene terephthalate, etc., treated paper, woodfree paper, glassine paper, etc., or laminated paper of woodfree paper or glassine paper and polyolefin, etc. Can be
- the thickness of the releasing liner usually 1 0 to 2 0 0 t / m, preferably 5 0-1 0 0 ⁇ m 0
- the dose of the transdermal formulation of the present invention in the prevention and treatment of premature birth and premature birth and dysuria depends on the patient's age, body weight, symptoms, etc.
- the preparation containing 0.1 to 500 mg is applied to 1 to 100 cm 2 of skin skin once a day to about once every 7 days.
- parts and% mean parts by weight and% by weight, respectively.
- the fatty acid salt of 2-tert-butylamino-1- (2-chloro-4-hydroxyhydroxy) ethane-1-ol which is a component of the transdermal absorption preparation of the present invention, can be produced by a conventional method, and has the following properties. Having.
- Example 2 To the acrylyl-based pressure-sensitive adhesive solution obtained in Example 1, (1) 1-2-tert-butylamino 1- (2-chloro-1-4-hydroquinpheninole) ethane-1-oneole tartrate and base Triethanolamine was added as a pH adjuster so that the amount of each to be incorporated into the plaster layer was 10%, mixed, and thoroughly stirred. A transdermal preparation of the invention was obtained.
- Example 6 70 parts of 2-ethylhexyl acrylate and 30 parts of methyl methacrylate were polymerized in ethyl acetate under an inert gas atmosphere to prepare an acryl-based pressure-sensitive adhesive solution containing no carboxyl group. To this solution was added (1-)-1-tert-butylamino-I- (2-chloro-4-hydroxypheninole) ethane-1-ol so that the content S in the plaster layer was 10%. After mixing and stirring sufficiently, the mixture was applied on a release liner so as to have a thickness of 40 // m after drying, and dried to form a plaster layer. Next, the body layer was adhered to a support (a polyester film having a thickness of 12 m) to obtain a transdermal absorption-type preparation of the present invention.
- a support a polyester film having a thickness of 12 m
- Example 2 In place of the acryl-based pressure-sensitive adhesive solution of Example 1, 95 parts of 2-ethylhexyl acrylate and 5 parts of acrylic acid were added with an inert gas; A percutaneous absorption-type preparation was obtained in the same manner as in Example 1, except that an acryl-based pressure-sensitive adhesive solution containing a carboxyl group, which was obtained by polymerization in ethyl acetate under ambient atmosphere, was used.
- High molecular weight polyisobutylene (viscosity average molecular weight 2,100,000, VISTANEX ⁇ 140, manufactured by Exxon Chemical Co., Ltd.) 50 parts, medium molecular weight polyisobutylene (viscosity average molecular weight 60,000, HIMOL 6H, manufactured by Nippon Petrochemical Co., Ltd.) 3 0 parts and alicyclic petroleum resin (100 ° C, Alcon P-100, Arakawa Chemical Co., Ltd.) 20 parts are dissolved in hexane, and the solution containing the high molecular weight rubber component is dissolved. Prepared.
- Example 8 In the solution of the high molecular weight rubber component-containing material obtained in Example 7, (_)-2-tert-butylamino-111- (2-chloro-4-hydroxydroxyphenyl) ethane-1-all-tartrate salt was added as an additive. Addition and mixing of isopropyl ristate (fatty acid ester) and trietanolamine as a pH regulator so that the blending amounts in the plaster layer become 10%, 40% and 10%, respectively. After sufficient stirring, a transdermal preparation of the present invention was obtained in the same manner as in Example 7.
- high molecular weight polyisobutylene (viscosity average molecular weight 990,000, VISTANBX MM-80, manufactured by Exxon Chemical Co., Ltd.) 37.5 parts, medium molecular weight polyisobutylene (viscosity average molecular weight 40,000, HIMOL 4H, Nippon Petrochemical Co., Ltd.
- SBS styrene butadiene-styrene block copolymer
- Example 7 A transdermal preparation of the present invention was obtained in the same manner as in Example 7, except for the above.
- Example 7 To the solution containing the high-molecular-weight rubber component obtained in Example 7, was added (1-1) 2-tert-butylamino-1-1 (2-chloro-1-4-hydroxyphenyl) ethane-1-ol After adding and mixing the prillate so that the blending amount in the plaster layer becomes 10% and sufficiently stirring, a transdermal preparation of the present invention was obtained in the same manner as in Example 7. .
- a transdermal preparation was obtained in the same manner as in Example 7, except that the additive (isopropyl myristate) was not added.
- the percutaneous absorption-type preparations obtained in Examples 1 to 13 and Comparative Examples 1 and 2 are punched into 6 mm ⁇ , and molted to 16 mm in diameter. Attach it to the center of the skin, and use the Automatic Flow Thru Diffusion Cell Appar atus, Vangard International Co., Ltd. W (set this, and settle the reception of the compound) ffl! ji
- the amount of the compound permeated into the water was measured by liquid chromatography. Changes in the amount over time are shown in FIGS. 1 and 2.
- Example 1 Example 2
- Example 3 Example 4
- Example 5 Example 6
- Example 11 Comparative Example 1 2-Ethyl acrylate 45 5 parts 4 5 parts 4 5 parts 90 parts 75 parts 7 0 parts 4 5 parts 9 5 parts Acrylic acid t FD kishetil 10 parts
- Examples 7 to] The transdermal preparations obtained in 0, 12 to 13 and Comparative Examples 2 to 3 were cut to a width of 2 Omm and a length of 5 Omm, and placed on the back of a pre-hair-deprived egret. After sticking for 6 hours, peeling was performed in the direction of 180 degrees at a speed of 100 mm, and the peel strength was measured. Further, the adhesive residue on the skin surface after separation was visually evaluated. Table 3 shows the results.
- the present compound contained in the plaster layer is continuously released to the skin surface and migrates into the blood, and its effective blood concentration lasts for a long time. Therefore, the preparation of the present invention is useful as a percutaneous absorption-type preparation in the prevention and treatment of urinary disorders such as impending flow, premature birth, and urinary incontinence.
- urinary disorders such as impending flow, premature birth, and urinary incontinence.
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Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU43209/97A AU4320997A (en) | 1996-09-26 | 1997-09-25 | Percutaneous preparations |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP8/254293 | 1996-09-26 | ||
JP25429396 | 1996-09-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998013035A1 true WO1998013035A1 (fr) | 1998-04-02 |
Family
ID=17262967
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1997/003412 WO1998013035A1 (fr) | 1996-09-26 | 1997-09-25 | Preparations percutanees |
Country Status (2)
Country | Link |
---|---|
AU (1) | AU4320997A (fr) |
WO (1) | WO1998013035A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0891782A3 (fr) * | 1997-07-17 | 2000-09-13 | Nitto Denko Corporation | Feuille adhésive médicale et sa procédé de fabrication |
WO2002038139A1 (fr) * | 2000-11-07 | 2002-05-16 | Hisamitsu Pharmaceutical Co., Inc. | Preparation pharmaceutique du type a absorption percutanee |
US10568845B2 (en) | 2001-08-24 | 2020-02-25 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system with fentanyl or related substances |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63104913A (ja) * | 1986-10-21 | 1988-05-10 | Teikoku Seiyaku Kk | 外用貼付剤 |
JPH0769869A (ja) * | 1993-08-27 | 1995-03-14 | Nitto Denko Corp | ブニトロロール含有貼付製剤 |
-
1997
- 1997-09-25 AU AU43209/97A patent/AU4320997A/en not_active Abandoned
- 1997-09-25 WO PCT/JP1997/003412 patent/WO1998013035A1/fr active Application Filing
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63104913A (ja) * | 1986-10-21 | 1988-05-10 | Teikoku Seiyaku Kk | 外用貼付剤 |
JPH0769869A (ja) * | 1993-08-27 | 1995-03-14 | Nitto Denko Corp | ブニトロロール含有貼付製剤 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0891782A3 (fr) * | 1997-07-17 | 2000-09-13 | Nitto Denko Corporation | Feuille adhésive médicale et sa procédé de fabrication |
WO2002038139A1 (fr) * | 2000-11-07 | 2002-05-16 | Hisamitsu Pharmaceutical Co., Inc. | Preparation pharmaceutique du type a absorption percutanee |
US10568845B2 (en) | 2001-08-24 | 2020-02-25 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system with fentanyl or related substances |
US10583093B2 (en) | 2001-08-24 | 2020-03-10 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system with fentanyl or related substances |
US10940122B2 (en) | 2001-08-24 | 2021-03-09 | Lts Lohmann Therapie-Systeme Ag | Transdermal therapeutic system with fentanyl or related substances |
Also Published As
Publication number | Publication date |
---|---|
AU4320997A (en) | 1998-04-17 |
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